Transformative Leadership Conversations with Winnie da Silva

Winnie da Silva

Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

  1. Think Differently. Transform How You Lead with Winnie da Silva

    APR 8

    Think Differently. Transform How You Lead with Winnie da Silva

    “Most leadership problems aren’t what they seem.” - Winnie da Silva You might think the issue in front of you is the real problem… but what if it’s just the surface? This season, I’m shifting things a bit. Instead of longer guest conversations, I’m bringing you shorter, more focused episodes designed to help you think more clearly, challenge your assumptions, and take immediate action in your leadership. Because the truth is, most leadership challenges aren’t as straightforward as they seem, and if we don’t slow down and look deeper, we risk solving the wrong problem entirely. In this episode, I’m setting the stage for what’s ahead and sharing why this shift matters, especially if you’re navigating complex, messy, real-world leadership situations. You’ll hear me discuss: Why many leadership problems are often misdiagnosed at first glanceWhat tends to sit beneath common challenges like performance issues or communication breakdownsHow unexamined assumptions and internal narratives can quietly shape your leadership effectivenessWhy solving only what’s visible can lead you to miss the bigger issueThe idea that leadership isn’t about fixing people, but about addressing root causesHow asking better questions can become your most powerful leadership toolWhat it looks like to adapt your leadership approach based on people and contextThe frameworks I use with clients to build trust, experiment, and lead more intentionallyHow this season is designed to give you practical, usable insights you can apply right away Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    5 min
  2. Freedom Firm: Rescue, Restoration, Justice with Leah Henck

    MAR 18

    Freedom Firm: Rescue, Restoration, Justice with Leah Henck

    Today's episode includes a discussion of child sex trafficking and sexual exploitation. While our goal is awareness and prevention, some listeners may find this topic difficult. Please take care of yourself and feel free to pause or skip this episode if needed. “Rescuing one girl matters - because that one life can change the future of an entire family.” - Leah Henck How does trafficking continue to thrive in plain sight - even in places with laws designed to stop it? In this special episode, I sit down with Leah Henck, President of Freedom Firm USA, to talk about the reality of child sex trafficking in India and the long, persistent work required to fight it. Freedom Firm partners with law enforcement, the courts, and social workers to rescue girls, support their healing, and pursue justice against those responsible. Leah shares powerful stories from the field and explains why real change requires more than rescue. It also requires addressing the systems that allow exploitation to continue. You’ll hear us discuss: How Freedom Firm began and why its mission focuses on rescue, restoration, and justiceWhy rescuing girls alone isn’t enough without changing the systems that allow trafficking to continueHow traffickers often move girls across regions or countries to isolate and control themWhat it takes to work with police and the judicial system in places where trafficking has been normalized for decadesThe emotional and practical challenges girls face after being rescuedWhy every survivor’s path to healing looks differentHow convictions against traffickers can slowly change an entire regionThe role vulnerability plays in trafficking everywhere, including in the United StatesWhy community awareness and support are critical in preventing exploitationHow one rescued girl can break a cycle that may have existed in her family for generations Resources Leah Henck on Freedom Firm | Freedom Firm Facebook | Freedom Firm Instagram | Sign up for Monthly Impact Update Email | Email: leah@freedomfirm.org Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    1h 15m
  3. Tiny Experiments in Leadership Thinking with Winnie da Silva

    12/29/2025

    Tiny Experiments in Leadership Thinking with Winnie da Silva

    “Leadership growth doesn’t have to come from huge reinventions. Often, it comes from tiny experiments.” Busyness has a sneaky way of convincing us that it equals importance - and for a long time, I let that idea drive how I measured my value as a leader. In this bonus episode, I’m sharing what happened when I decided to interrupt that pattern with one small, intentional experiment. No grand strategy. No perfectly mapped plan. Just 45 minutes a week to think - really think - and see what surfaced. You’ll hear me discuss: How I realized I was buying into the belief that my leadership value is tied to productivityWhy I committed to a short, weekly strategic thinking practice and what I hoped it might changeHow strange and uncomfortable it felt at first to sit with no agenda, no screen, and no clear outcomeWhy even 30 minutes of protected thinking time turned out to be more than enoughHow rest, reflection, and permission played a bigger role than I expectedWhat I noticed about my thinking carrying over and deepening between sessionsWhy sticking to pen and paper helped me trust my own thinking instead of outsourcing itHow one meaningful conversation with a trusted colleague reshaped my strategic clarityWhy strategic thinking doesn’t have to be a solo activity to be effectiveWhat consistency, accountability, and keeping the bar low actually made possible Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    15 min
  4. How Leadership Confidence Gets Tested with Winnie da Silva

    12/17/2025

    How Leadership Confidence Gets Tested with Winnie da Silva

    “When leaders lose confidence, it’s usually traced back to these four patterns: the unknown, the comparison, the undermining relationship, and the identity transition.” Confidence doesn’t usually disappear overnight. More often, it slips away quietly, shaped by patterns we don’t always notice while we’re inside them. After two decades of coaching leaders, building teams, and watching incredibly capable people question themselves, I started to see the same confidence breakdowns show up again and again. In this episode, I’m wrapping up The Confidence to Lead series by sharing the four patterns I see most often when leadership confidence starts to erode and what it actually takes to rebuild it from the inside out. You’ll hear me discuss: How operating in the unknown erodes confidence when expectations are unclear, success isn’t defined, and feedback feels vague or inconsistentWhy comparison quietly undermines leadership confidence, especially when we measure ourselves against someone else’s style, presence, or definition of successHow undermining relationships and low psychological safety can wear down even the strongest leaders over timeWhy identity transitions - like promotions, role changes, or industry shifts - often trigger self-doubt, even when you’re fully qualifiedReal client stories that show how these patterns play out in everyday leadership momentsThe questions I use in coaching to help leaders identify which pattern might be impacting them mostPractical ways to rebuild confidence in each situation, without waiting for permission, validation, or perfect conditions Resources Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    26 min
  5. The Confidence You Learn with Dr. Angela Stopper

    12/10/2025

    The Confidence You Learn with Dr. Angela Stopper

    “Confidence is a skill. It is a skill just like every other skill that we have, that we can use, that we practice.” - Dr. Angela Stopper Confidence can feel so uneven. Solid in one moment and shaky in the next. It’s one of those topics that shows up in almost every leadership conversation I have, yet most of us still aren’t quite sure how it actually works. Is it innate? Is it something you earn? Or does it grow through experience? In this episode, I sit down with Dr. Angela Stopper, Chief Learning Officer at UC Berkeley, who has spent years looking at confidence from a completely different angle. Angela sees confidence as a skill - a set of competencies we can practice, strengthen, and shape so it feels authentic to who we are. Her model makes the entire idea of “being confident” feel far more doable and a lot less mysterious. You'll hear us discuss: Why treating confidence as a skill makes it accessible to literally everyoneThe six competencies in Angela’s model and how they work togetherThe many ways the “confidence gap” shows up and why it isn’t just a gender issueHow outside reactions, expectations, and bias can shape our sense of confidenceThe pressure to not be “too much,” especially for women, and how Angela coaches people through thatThe role courage plays in leadership and why it’s often misunderstoodThe connection between confidence and making decisions, even when the outcome isn’t guaranteedHow mistakes and small experiments build resilience and help confidence grow over time Resources Angela Stopper on LinkedIn Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    43 min
  6. Confidence You Build, Not Find with Julienne H. Silverman

    12/03/2025

    Confidence You Build, Not Find with Julienne H. Silverman

    “It’s not that you already know the answers or already are perfect at something, but that you believe that you can get there.” - Julienne Silverman Confidence can look rock–solid from the outside… but inside, it’s usually a mix of courage, doubt, experience, improvisation, and a whole lot of personal growth. And sometimes the biggest boosts to our confidence come from the moments we’d never expect. In this episode, I sit down with investment banking executive Julienne (Julie) Silverman for a truly grounded and honest conversation about what confidence actually feels like and how it evolves over the course of a career. Julie shares stories from her early days managing the legendary New York restaurant Pastis all the way through her senior roles on Wall Street today, and she opens up about the shifts, pivots, and lessons that shaped her leadership. You’ll hear us discuss: How Julie defines confidence in a way that feels surprisingly freeing and why it has nothing to do with perfection.The unforgettable Courtney Love story that taught her how to handle pressure and trust her instincts long before she worked in finance.What the “arc of confidence” looks like and why confidence often dips when you step into bigger, more challenging roles.How she navigates ambiguity in entrepreneurial environments while keeping both daily decisions and long-term goals in view.The subtle, gendered expectations around confidence at work and the small habits that help women show up with more presence.Julie’s go-to advice for younger women: introduce yourself with your full name, take a literal seat at the table, and own your spot in the room.Why being fully out at work has strengthened her leadership, and how authenticity creates deeper relationships and real confidence Resources Julienne H. Silverman on LinkedIn | On the Web Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org

    45 min

Trailers

4.7
out of 5
20 Ratings

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Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

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